Screening of indeno[1,2-b]indoloquinones by MALDI-MS: a new set of potential CDC25 phosphatase inhibitors brought to light

J Enzyme Inhib Med Chem. 2016;31(sup3):25-32. doi: 10.1080/14756366.2016.1201480. Epub 2016 Jun 30.

Abstract

Quinones and quinones-like compounds are potential candidates for the inhibition of CDC25 phosphatases. The combination of MALDI-MS analyses and biological studies was used to develop a rapid screening of a targeted library of indeno[1,2-b]indoloquinone derivatives. The screening protocol using MALDI-TOFMS and MALDI-FTICRMS highlighted four new promising candidates. Biological investigations showed that only compounds 5c-f inhibited CDC25A and -C phosphatases, with IC50 values around the micromolar range. The direct use of a screening method based on MALDI-MS technology allowed achieving fast scaffold identification of a new class of potent inhibitors of CDC25 phosphatases. These four molecules appeared as novel molecules of a new class of CDC25 inhibitors. Assessment of 5c-e in an MRC5 proliferation assay provided an early indicator of toxicity to mammalian cells. Compound 5d seems the most promising hit for developing new CDC25 inhibitors.

Keywords: CDC25 inhibitors; MALDI mass spectrometry; indeno[1,2-b]indoloquinones; irreversibility.

MeSH terms

  • Cell Line
  • Cell Proliferation / drug effects
  • Cell Survival / drug effects
  • Dose-Response Relationship, Drug
  • Drug Evaluation, Preclinical*
  • Enzyme Inhibitors / chemical synthesis
  • Enzyme Inhibitors / chemistry
  • Enzyme Inhibitors / pharmacology*
  • Humans
  • Indenes / chemical synthesis
  • Indenes / chemistry
  • Indenes / pharmacology*
  • Molecular Structure
  • Quinones / chemical synthesis
  • Quinones / chemistry
  • Quinones / pharmacology*
  • Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization
  • Structure-Activity Relationship
  • cdc25 Phosphatases / antagonists & inhibitors*
  • cdc25 Phosphatases / metabolism

Substances

  • Enzyme Inhibitors
  • Indenes
  • Quinones
  • indeno(1,2-b)indoloquinone
  • CDC25A protein, human
  • CDC25C protein, human
  • cdc25 Phosphatases